Portal de Periódicos da CAPES

Birch Reduction of (−)-Ephedrine. Formation of a New, Versatile Intermediate for Organic Synthesis

2004; American Chemical Society; Volume: 69; Issue: 16 Linguagem: Inglês

10.1021/jo049726u

1520-6904

Gury Zvilichovsky, Isra Gbara-Haj-Yahia,

Advanced Synthetic Organic Chemistry

The reduction of (-)-ephedrine by lithium in liquid ammonia resulted in the formation of S-1-(1,4-cyclohexadien-1-yl)-N-methyl-2-propanamine. In addition to the reduction of the aromatic ring, the hydroxy group was reduced as well. The resulting 1,4-cyclohexadienyl group is a potentially versatile intermediate for further synthetic transformations. The ozonolysis of this group was investigated, producing derivatives of beta-keto-delta-methylamino esters and beta-keto aldehydes which could be subsequently converted to heterocycles. The restriction to rotation of the C-N bond in N-benzoyl-1-(1,4-cyclohexadien-1-yl)-N-methyl-2-propanamine is described.